4-tert-Butylcyclohexylamine → HCID 178445668, compound

HRID 230021Notes

Reaction equation

HRID 230021 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.[C:12]([CH:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1)([CH3:15])([CH3:14])[CH3:13].[BH4-].[Na+]>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:17][CH2:18]1)[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 793964-tert-ButylcyclohexylamineHCID 5206955-Bromo-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 178445668HCID 178445668, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-bromoindan-1-one (6.33 g, 30.0 mmol), titanium (IV) isopropoxide (17.8 mL, 60.0 mmol), 4-tert-butylcyclohexyl amine (9.32 g, 60.0 mmol) in absolute ethanol (200 mL) was stirred under nitrogen at room temperature for 12 h. Sodium borohydride (1.70 g, 45.0 mmol) was then added and the resulting mixture was stirred for an additional 8 h at room temperature. The reaction was quenched by pouring into aqueous ammonia (2N, 300 mL). The resulting inorganic precipitate was filtered off and washed with dichloromethane (150 mL). The organic layer was separated and the remaining aqueous layer was extracted once with dichloromethane (150 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated. Chromatography (10% to 20% EtOAc in Hexane) afforded (5-Bromo-2,3-dihydro-1H-inden-1-yl)(trans-4-tert-butylcyclohexyl)amine and the corresponding cis product (less polar). HPLC/MS: m/z=350.1 (M+1), Rt=3.01 min.

Workup

  1. stirringthe resulting mixture was stirred for an additional 8 h at room temperature
  2. customThe reaction was quenched
  3. additionby pouring into aqueous ammonia (2N, 300 mL)
  4. filtrationThe resulting inorganic precipitate was filtered off
  5. washwashed with dichloromethane (150 mL)
  6. customThe organic layer was separated
  7. extractionthe remaining aqueous layer was extracted once with dichloromethane (150 mL)
  8. dry with materialThe combined organic extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-cbdd220f31cd472dbcbcd71ca0e3cd53
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

Loading…